CA2481909C - Preparation d'analogues alkyl-24 de cholecalciferol - Google Patents

Preparation d'analogues alkyl-24 de cholecalciferol Download PDF

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Publication number
CA2481909C
CA2481909C CA2481909A CA2481909A CA2481909C CA 2481909 C CA2481909 C CA 2481909C CA 2481909 A CA2481909 A CA 2481909A CA 2481909 A CA2481909 A CA 2481909A CA 2481909 C CA2481909 C CA 2481909C
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CA
Canada
Prior art keywords
group
formula
configuration
groups
hydrogen atom
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related
Application number
CA2481909A
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English (en)
Other versions
CA2481909A1 (fr
Inventor
Andrzej Kutner
Jacek Martynow
Michal Chodynski
Wieslaw Szelejewski
Hanna Fitak
Malgorzata Krupa
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Instytut Farmaceutiyczny
Original Assignee
Instytut Farmaceutiyczny
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from PL353328A external-priority patent/PL195726B1/pl
Priority claimed from PL353832A external-priority patent/PL210106B1/pl
Application filed by Instytut Farmaceutiyczny filed Critical Instytut Farmaceutiyczny
Publication of CA2481909A1 publication Critical patent/CA2481909A1/fr
Application granted granted Critical
Publication of CA2481909C publication Critical patent/CA2481909C/fr
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C31/13—Monohydroxylic alcohols containing saturated rings
    • C07C31/133—Monohydroxylic alcohols containing saturated rings monocyclic
    • C07C31/1333—Monohydroxylic alcohols containing saturated rings monocyclic with a three-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63—Esters of sulfonic acids
    • C07C309/72—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/73—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C401/00—Irradiation products of cholesterol or its derivatives; Vitamin D derivatives, 9,10-seco cyclopenta[a]phenanthrene or analogues obtained by chemical preparation without irradiation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • C07F7/1872—Preparation; Treatments not provided for in C07F7/20
    • C07F7/1892—Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Cette invention a trait à un procédé de préparation d'analogues alkyl-24 de cholécalcyférol, correspondant à la formule (I), ayant une configuration (5E) ou (5Z). Dans cette formule, X représente un atome d'hydrogène, un groupe hydroxy ou un groupe OR¿1?, R¿1?, R¿2? et R¿3?, qui peuvent être identiques ou différents, représentent des groupes adaptés à la protection hydroxy, R4 représente une chaîne alkyle ou un groupe cycloalkyle ayant de 1 à 6 atomes de carbone, éventuellement substitué par des groupes alkyle ayant de 1 à 3 atomes de carbone, notamment le calcipotriol. Cette invention porte également sur de nouveaux composés non racémiques, en l'occurrence des synthons, des plus utiles pour la synthèse de substances actives du point de vue pharmacologique.
CA2481909A 2002-04-11 2003-04-10 Preparation d'analogues alkyl-24 de cholecalciferol Expired - Fee Related CA2481909C (fr)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
PLP.353328 2002-04-11
PL353328A PL195726B1 (pl) 2002-04-11 2002-04-11 Sposób otrzymywania 24-alkilowych analogów cholekalcyferolu oraz nowe związki wyjściowe
PLP.353832 2002-05-12
PL353832A PL210106B1 (pl) 2002-05-12 2002-05-12 Sposób otrzymywania nieracemicznych syntonów cyklopropanowych i związki pośrednie
PCT/PL2003/000037 WO2003087048A2 (fr) 2002-04-11 2003-04-10 Preparation d'analogues alkyl-24 de cholecalciferol et de composes non racemiques

Publications (2)

Publication Number Publication Date
CA2481909A1 CA2481909A1 (fr) 2003-10-23
CA2481909C true CA2481909C (fr) 2013-07-02

Family

ID=29253775

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2481909A Expired - Fee Related CA2481909C (fr) 2002-04-11 2003-04-10 Preparation d'analogues alkyl-24 de cholecalciferol

Country Status (5)

Country Link
US (1) US7915241B2 (fr)
EP (1) EP1497264A2 (fr)
AU (1) AU2003262179A1 (fr)
CA (1) CA2481909C (fr)
WO (1) WO2003087048A2 (fr)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2481909C (fr) 2002-04-11 2013-07-02 Instytut Farmaceutyczny Preparation d'analogues alkyl-24 de cholecalciferol
PL208188B1 (pl) 2007-07-12 2011-03-31 Inst Farmaceutyczny Sposób otrzymywania kalcypotriolu
ES2234423B1 (es) * 2003-12-05 2006-03-01 Laboratorios Viñas, S.A. Procedimiento para la obtencion de derivados de vitamina d a partir de compuestos monohalogenovinilicos.
PL203052B1 (pl) * 2004-05-14 2009-08-31 Inst Farmaceutyczny Sposób otrzymywania sulfonylowych pochodnych cholekalcyferolu i nowe związki pośrednie wyodrębniane w tym sposobie
TW200714580A (en) * 2005-10-14 2007-04-16 Formosa Lab Inc Process for preparing vitamin D analogs
WO2008027532A2 (fr) * 2006-08-29 2008-03-06 Teva Pharmaceutical Industries Ltd. Compositions actives pharmacologiquement stables à base de vitamine d et de corticostéroïdes, compatibles avec un faible ph
CN101906443B (zh) * 2010-06-25 2012-07-25 绍兴文理学院 (2S)-[2-(t-叔丁基)二甲基硅氧基]-2-环丙基-1-乙基-三苯基膦的合成方法
CN105753758B (zh) * 2014-12-17 2017-11-03 上虞京新药业有限公司 卡泊三醇的制备方法
CN107643354B (zh) * 2016-07-22 2022-02-01 重庆华邦胜凯制药有限公司 卡泊三醇起始原料a及相关杂质的分离与测定方法
CN115819773B (zh) * 2022-05-27 2023-10-03 浙江开化合成材料有限公司 一种分子量窄分布的耐高温苯甲基硅油的制备方法

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PH16989A (en) * 1978-11-07 1984-05-04 Res Inst Medicine Chem Process for the preparation of 1-hydroxylated vitamin d compounds
EP0070588B1 (fr) * 1981-07-17 1986-05-07 Duphar International Research B.V Procédé de préparation de dérivés de 1 alpha-hydroxy vitamine D ou de 1 alpha-hydroxy prévitamine D et d'adducts de prévitamine D ou de tachysterol avec des diénophiles appropriés
JPH07100685B2 (ja) * 1985-08-02 1995-11-01 レオ・ファ−マシュ−ティカル・プロダクツ・リミテッド・エイ／エス（レ−ベンス・ケミスケ・ファブリック・プロデュクチオンスアクチ−セルスカブ） 新規ビタミンｄ類似体
US4927815A (en) * 1988-04-29 1990-05-22 Wisconsin Alumni Research Foundation Compounds effective in inducing cell differentiation and process for preparing same
US5194431A (en) * 1992-07-08 1993-03-16 Wisconsin Alumni Research Foundation 24-cyclopropane vitamin D derivatives
DE19523389A1 (de) 1995-06-23 1997-01-09 Bayer Ag Enzymatische Methode zum oxidativen Abbau von fluoreszierenden Verbindungen
GB9526208D0 (en) * 1995-12-21 1996-02-21 Res Inst Medicine Chem Chemical compounds
PL188697B1 (pl) * 1998-01-14 2005-03-31 Inst Farmaceutyczny Sposób otrzymywania pochodnych cholekalcyferolu oraz nowe związki pośrednie
CA2481909C (fr) 2002-04-11 2013-07-02 Instytut Farmaceutyczny Preparation d'analogues alkyl-24 de cholecalciferol

Also Published As

Publication number Publication date
WO2003087048A2 (fr) 2003-10-23
CA2481909A1 (fr) 2003-10-23
AU2003262179A1 (en) 2003-10-27
AU2003262179A8 (en) 2003-10-27
WO2003087048A3 (fr) 2004-03-18
US7915241B2 (en) 2011-03-29
EP1497264A2 (fr) 2005-01-19
US20050119241A1 (en) 2005-06-02

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